Ethyl bromoacetate → ethyl 2-(2-((N-methylcarbamoyl)methyl)phenoxy)acetate

HRID 366127Notes

Reaction equation

HRID 366127 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([NH:17][CH3:18])=[O:16].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O.[I-].[K+]>[CH3:18][NH:17][C:15]([CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:16]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 217123112-(2-hydroxyphenyl)-N-methylacetamide

Product 1

HCID 10848339ethyl 2-(2-((N-methylcarbamoyl)methyl)phenoxy)acetateYield 103%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

Potassium carbonate (2.81 g, 20.34 mmol) was given to a solution of 2-(2-hydroxyphenyl)-N-methylacetamide (3.36 g, 20.34 mmol) in acetone (150 ml). Ethyl bromoacetate (2.13 ml, 19.32 mmol) and potassium iodide (166 mg, 1.02 mmol) were added successively. The reaction mixture was heated to reflux for 6 h. It was left at room temperature for 16 h. The solid was filtered off. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (80 g), using ethyl acetate/dichloromethane (1:1) as eluent, to give 5.00 g of ethyl 2-(2-((N-methylcarbamoyl)methyl)phenoxy)acetate.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. filtrationThe solid was filtered off
  4. customThe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (80 g)

Sources & evidence

ORD record
ord-d6255450bb824c50a533304e2e38faa5
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

Loading…